Gold-Catalyzed Proto- and Deuterodeboronation

Graeme Barker, Stacey Webster, David G Johnson, Rachel Curley, Matthew Andrews, Paul Christopher Young, Stuart A Macgregor, Ai-Lan Lee

Research output: Contribution to journalArticle

Abstract

A mild gold-catalyzed protodeboronation reaction, which does not require acid or base additives and can be carried out in "green" solvents, is described. As a result, the reaction is very functional-group-tolerant, even to acid- and base-sensitive functional groups, and should allow for the boronic acid group to be used as an effective traceless directing or blocking group. The reaction has also been extended to deuterodeboronations for regiospecific ipso-deuterations of aryls and heteroaryls from the corresponding organoboronic acid. Based on density functional theory calculations, a mechanism is proposed that involves nucleophilic attack of water at boron followed by rate-limiting B-C bond cleavage and facile protonolysis of a Au-σ-phenyl intermediate.

LanguageEnglish
Pages9807-9816
Number of pages10
JournalJournal of Organic Chemistry
Volume80
Issue number20
Early online date28 Jun 2015
DOIs
Publication statusPublished - 16 Oct 2015

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Gold
Functional groups
Acids
Boronic Acids
Boron
Density functional theory
Water

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Barker, G., Webster, S., Johnson, D. G., Curley, R., Andrews, M., Young, P. C., ... Lee, A-L. (2015). Gold-Catalyzed Proto- and Deuterodeboronation. Journal of Organic Chemistry, 80(20), 9807-9816. https://doi.org/10.1021/acs.joc.5b01041
Barker, Graeme ; Webster, Stacey ; Johnson, David G ; Curley, Rachel ; Andrews, Matthew ; Young, Paul Christopher ; Macgregor, Stuart A ; Lee, Ai-Lan. / Gold-Catalyzed Proto- and Deuterodeboronation. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 20. pp. 9807-9816.
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Barker, G, Webster, S, Johnson, DG, Curley, R, Andrews, M, Young, PC, Macgregor, SA & Lee, A-L 2015, 'Gold-Catalyzed Proto- and Deuterodeboronation', Journal of Organic Chemistry, vol. 80, no. 20, pp. 9807-9816. https://doi.org/10.1021/acs.joc.5b01041

Gold-Catalyzed Proto- and Deuterodeboronation. / Barker, Graeme; Webster, Stacey; Johnson, David G; Curley, Rachel; Andrews, Matthew; Young, Paul Christopher; Macgregor, Stuart A; Lee, Ai-Lan.

In: Journal of Organic Chemistry, Vol. 80, No. 20, 16.10.2015, p. 9807-9816.

Research output: Contribution to journalArticle

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AU - Macgregor, Stuart A

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Barker G, Webster S, Johnson DG, Curley R, Andrews M, Young PC et al. Gold-Catalyzed Proto- and Deuterodeboronation. Journal of Organic Chemistry. 2015 Oct 16;80(20):9807-9816. https://doi.org/10.1021/acs.joc.5b01041